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Facile synthetic approaches for new series of pyrazole-4-carbonitrile derivatives

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Abstract

Aldol condensation of 3-acetyl-1-(4-fluorophenyl)-5-phenyl-1H-pyrazole-4-carbonitrile with benzaldehyde afforded 1-(4-fluorophenyl)-5-phenyl-3-((E)-3-phenylacryloyl)-1H-pyrazole-4-carbonitrile, which in turn reacted with a series of 1,2- and 1,3-binucleophiles to afford new substituted pyrazoles, pyrimidines, and condensed azolopyrimidine derivatives attached to pyrazole scaffold at position 3. Moreover, multicomponent condensation reactions (MCRs) were used as an alternative method, and 1H–13C heteronuclear single quantum coherence (HSQC) in addition to heteronuclear multiple-bond correlation (HMBC) spectra were used for full confirmation of a selected example of these compounds. The reactivity of 1-(4-fluorophenyl)-5-phenyl-3-((E)-3-phenylacryloyl)-1H-pyrazole-4-carbonitrile towards active methylene derivatives, including malononitrile and ethyl cyanoacetate, was explored and afforded 2-amino-6-(4-cyano-1-(4-fluorophenyl)-5-phenyl-1H-pyrazol-3-yl)-4-phenylpyridine-3-carbonitrile and ethyl 6-(4-cyano-1-(4-fluorophenyl)-5-phenyl-1H-pyrazol-3-yl)-1,2-dihydro-2-oxo-4-phenylpyridine-3-carboxylate, respectively.

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References

  1. P. Jayaroopa, G.l Vasanth Kumar, N. Renuka, M.A. Harish Nayaka, K. Ajay Kumar, Int. J. Pharm. Tech. Res. 5, 264–270 (2013)

    Google Scholar 

  2. G. Mariappan, B.P. Saha, L. Sutharson, A. Haldar, Ind. J. Chem. Sect. B 49, 1671–1674 (2010)

    Google Scholar 

  3. S. Shyama, A. Robert, S. Ying, N. Sonoko, B. Brown, L. Jose, S. Eduard, D.P.C. Nicholas, Bioorg. Med. Chem. Lett. 19, 222–225 (2009)

    Article  Google Scholar 

  4. M. Govindaraju, G. Vasanth Kumar, G. Pavithra, M. Harish, A. Nayaka, B.N. Mylarappa, S. Eduard, K. Ajay Kumar, IOSR J. Pharm. Biol. Sci. 2, 30–34 (2012)

    Google Scholar 

  5. R. Kalirajan, R. Leela, S. Jubie, B. Gowramma, S. Gomathi, S. Sankar, Ind. J. Chem. Sect. B 50, 1794–1799 (2013)

    Google Scholar 

  6. A.M. Farag, A.S. Mayhoub, T.M. El-Debss, A.E. Amr, K.A. Ali, N.A. Abdel-Hafez, M.M. Abdulla, Arch. Pharm. Chem. 343, 384–396 (2010)

    Article  CAS  Google Scholar 

  7. A.M. Farag, K.A. Ali, T.M. El-Debss, A.S. Mayhoub, A.E. Amr, N.A. Abdel-Hafez, M.M. Abdulla, Eur. J. Med. Chem. 45(12), 5887–5898 (2010)

    Article  CAS  Google Scholar 

  8. M.H. Elnagdi, M.R.H. Elmoghayar, G.E. Elgemeie, Synthesis, 1,  1–7 (1984)

  9. M.M. Abdel-Khalik, S.M. Agamya, M.H. Elnagdi, Z. Naturforsch. 55, 1211–1215 (2000)

    Article  CAS  Google Scholar 

  10. E.V. Burgaz, M.A. Yilmaz, T. Pekel, A. Oktemer, Tetrahedron 63, 7229–7239 (2007)

    Article  CAS  Google Scholar 

  11. V.A. Chebanov, S.M. Desenko, Curr. Org. Chem. 10, 297–317 (2006)

    Article  CAS  Google Scholar 

  12. K.A. Ali, Arkivoc. 11, 55–63 (2010)

  13. K.A. Ali, E.A. Ragab, G. Mloston, M. Celeda, A. Lindend, H. Heimgartner, Helv. Chim. Acta 96, 633–643 (2013)

    Article  CAS  Google Scholar 

  14. K.A. Ali, H.S. Abdalghfar, K. Mahmoud, E.A. Ragab. J. Heterocycl. Chem. 50(5), 1157–1164 (2013)

    CAS  Google Scholar 

  15. A.E. Amr, K.A. Ali, M.M. Abdalla, Eur. J. Med. Chem. 44, 901–907 (2009)

    Article  CAS  Google Scholar 

  16. K.A. Ali, H.M. Hosni, E.A. Ragab, S.I. Abd El-Moez, Arch. Pharm. Chem. 345(3), 231–239 (2012)

    Article  CAS  Google Scholar 

  17. D.G. Powers, D.S. Casebier, D. Fokas, W.J. Ryan, J.R. Troth, D.L. Coffen, Tetrahedron 54, 4085–4096 (1998)

    Article  CAS  Google Scholar 

  18. P. Wolkoff, Can. J. Chem. 53, 1333–1335 (1975)

    Article  CAS  Google Scholar 

  19. A.F. Hegarty, M.P. Cashoman, F.L. Scoti, J. Chem. Soc. D 13, 684–685 (1971)

    Article  Google Scholar 

  20. K.M. Dawood, E.A. Ragab, A.M. Farag, J. Chem. Res. 11, 1151–1160 (2003)

    Google Scholar 

Download references

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Authors and Affiliations

  1. Applied Organic Chemistry Department, Center of Excellence for Advanced Science, National Research Centre, Dokki, Giza, 12622, Egypt

    Korany A. Ali & Heba S. Abdelghafar

  2. Departments of Chemistry, Faculty of Science, Cairo University, Giza, 12613, Egypt

    Eman Ali Ragab & Ahmad M. Farag

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  1. Korany A. Ali
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  2. Eman Ali Ragab
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  3. Heba S. Abdelghafar
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  4. Ahmad M. Farag
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Correspondence to Korany A. Ali.

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Ali, K.A., Ragab, E.A., Abdelghafar, H.S. et al. Facile synthetic approaches for new series of pyrazole-4-carbonitrile derivatives. Res Chem Intermed 42, 3553–3566 (2016). https://doi.org/10.1007/s11164-015-2231-y

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